Matt Dillon, Patrick Swayze, Tom Cruise

The greasers in The Outsiders didn't have matching, color-coordinated outfits, knuckle-tweaking gang signs or chrome-plated .45s. What they did have was a strong sense of brotherhood, loyalty and really oily, slicked back hair. That's all you needed to be cool back in the '60s, the simple, innocent decade that provides the idyllic backdrop for this decidedly disenchanting film from acclaimed director Francis Ford Coppola (Godfather, Apocalypse Now). A slew of manly '80s stars (from Swayze and Estevez to Lowe and Cruise) play the aforementioned greasers who get caught up in some unpleasantness with a richer, less grimy gang. The end result is murder and mayhem on the Midwest plains.
Why you should rent it:

Watching this movie allows you to see what you missed when you skipped out on reading this book in high school.

Ice Cube, Angela Bassett, Cuba Gooding Jr.

Ice Cube is an example of the American Dream on steroids. He went from slinging dope in a gang to starring in fluffy Hollywood family comedies in just a few years. But before he sold out, he played it real as a ruthless gang member from LA's infamous Compton neighborhood in this seminal 1991 gang classic. It came out just as the media was trumpeting the Crips and the Bloods as an unstoppable plague that would eventually destroy America. In response to the hysteria, director John Singleton presented the human side of the story and showed how poverty can trap even the unwilling in a cycle of violence.

James Dean, Natalie Wood, Dennis Hopper

As far as the movies would have us believe, all teenagers in the '50s banded together in rowdy packs, hell-bent on lawlessness and violence. Since those same good-for-nothing punk kids eventually became our parents, it certainly sounds like another case of classic Hollywood sensationalism. And no movie is a bigger culprit than this campy classic. James Dean mopes and scowls his way through a performance as a troublemaking teen who becomes the new kid in town. He must band together with some of the locals or end up with a switchblade in the heart or, worse yet, a lonely, friendless teenage existence.
Why you should rent it:

James Dean's performance as the immoral, devil-may-care Jim Stark seems outrageously dated half a century later, but it's certainly worth a laugh.

Marlon Brando, Mary Murphy, Lee Marvin

At their very best, bikers annoy us with obscenely loud mufflers. At their very worst, they are murderous thugs with little regard for the law. Marlon Brando and his fellow members of the Black Rebel Motorcycle Gang are definitely in the latter category. They descend on a small town, disrupt its friendly little motorcycle race and take over its bar. When a rival gang decides to join in on the fun, things really get interesting.

Why you should rent it:

Yes, there was a time when Brando was able to fit on a motorcycle. And he rides it with reckless abandon in this entertaining, if not a bit campy, gang classic.

The 51st state - Nice Wheels. Dirty Deals. And One Mean Mother In A Kilt. Have a nice trip

Gangs of New York - America Was Born In The Streets.

The Fast and the Furious - If loyalties must be broken, If the lines must be crossed, do it fast, do it Furious

Goodfellas - "As far back as I can remember, I've always wanted to be a gangster." -- Henry Hill, Brooklyn, N.Y. 1955.

Be Cool - Everyone is looking for the next big hit